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Synthesis of 3-Silylated 3-Sulfolenes from Propargylsilanes and their Reductive Desulfitation

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Chemistry of Heterocyclic Compounds Aims and scope

Protonation of propargylsilanes induces 1,2-silyl group shift and provides 2-silylated dienes. If this reaction is performed in liquid SO2, the diene formation is followed by instant cheletropic SO2 addition, and 3-silylated 3-sulfolenes are obtained. Liquid SO2 as polar and Lewis acidic reaction medium makes it possible to use relatively weak Brønsted acid catalysts such as H2O and benzoic acid. Depending on the starting material, reductive desulfitation of 3-silylated 3-sulfolenes provides vinyl, allyl, or aliphatic silanes.

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Authors and Affiliations

  1. Institute of Technology of Organic Chemistry, Faculty of Materials Science and Applied Chemistry, Riga Technical University, 3 P. Valdena St, Riga, LV-1048, Latvia

    Rūdolfs Beļaunieks, Mikus Puriņš, Viktors Kumpiņš & Māris Turks

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  1. Rūdolfs Beļaunieks
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  2. Mikus Puriņš
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  3. Viktors Kumpiņš
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  4. Māris Turks
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Correspondence to Māris Turks.

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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2021, 57(1), 20–25

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Beļaunieks, R., Puriņš, M., Kumpiņš, V. et al. Synthesis of 3-Silylated 3-Sulfolenes from Propargylsilanes and their Reductive Desulfitation. Chem Heterocycl Comp 57, 20–25 (2021). https://doi.org/10.1007/s10593-021-02862-1

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  • DOI: https://doi.org/10.1007/s10593-021-02862-1

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